Sodium Iodide → 4-[4-(Benzyloxy)butyl]-6-methoxypyrido[2,3-b]pyrazin-3(4H)-one

HRID 1847037Notes

Reaction equation

HRID 1847037 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[N:11]=[CH:10][C:9](=[O:12])[NH:8][C:7]=2[N:13]=1.[H-].[Li+].Br[CH2:17][CH2:18][CH2:19][CH2:20][O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.[I-].[Na+]>CN(C)C=O.C(OCC)(=O)C>[CH2:22]([O:21][CH2:20][CH2:19][CH2:18][CH2:17][N:8]1[C:9](=[O:12])[CH:10]=[N:11][C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[N:13][C:7]1=2)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 62714Lithium hydrideHCID 4422181((4-Bromobutoxy)methyl)benzeneHCID 667398036-Methoxypyrido[2,3-B]pyrazin-3(4H)-one

Product 1

HCID 867249624-[4-(Benzyloxy)butyl]-6-methoxypyrido[2,3-b]pyrazin-3(4H)-oneYield 74%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

In N,N-dimethylformamide (15 ml) was dissolved 6-Methoxypyrido[2,3-b]pyrazin-3(4H)-one (600 mg, 3.39 mmol). The solution was cooled in an ice bath, lithium hydride (purity 90%, 35.9 mg, 4.06 mmol) was then added thereto and the mixture was stirred at room temperature for 40 minutes. The reaction solution was cooled again in an ice bath, benzyl 4-bromobutyl ether (0.774 ml, 4.06 mmol) and sodium iodide (609 g, 4.06 mmol) were added and then the mixture was stirred overnight at room temperature. The reaction solution was diluted with ethyl acetate, washed sequentially with saturated sodium chloride solution (2×), water and saturated sodium chloride solution, dried over anhydrous magnesium sulfate and the solvent was removed under reduced pressure. The obtained residue was purified by silica gel column chromatography (n-hexane/ethyl acetate) to yield 847 mg (74%) of the title compound in the form of a light yellow syrup.

Workup

  1. temperatureThe solution was cooled in an ice bath
  2. temperatureThe reaction solution was cooled again in an ice bath
  3. stirringthe mixture was stirred overnight at room temperature
  4. washwashed sequentially with saturated sodium chloride solution (2×), water and saturated sodium chloride solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was removed under reduced pressure
  7. customThe obtained residue was purified by silica gel column chromatography (n-hexane/ethyl acetate)

Sources & evidence

ORD record
ord-931ceb9b3eb548a3971227665a622668
Source dataset
uspto-grants-2015_02
Patent number
US08952010B2

Reaction notes

Loading…